4-Iodotoluene → HCID 11208981, compound

Participants

Reaction Steps

To the suspension of sodium hydride (60%, 1.2 g, 30 mmol) in 50 ml of anhydrous dioxane containing 3.5 ml of HMPA were added di-tert-butyl malonate (6.488 g, 30 mmol) and p-iodotoluene (1), the mixture was stirred at room temperature for 1 hour. To the resulting solution was added copper (I) bromide (5.163 g, 36 mmol, 1.2 equivalents), the mixture was heated at refluxing temperature. Then the reaction mixture was cooled to room temperature, 30 ml of saturated aqueous ammonium chloride solution was added to quench the reaction, and the product was extracted with ethyl acetate (50 ml×3), washed with brine, dried over sodium sulfate. The solvent was evaporated, and the oily residue obtained was purified by chromatography to give p-tolyl-malonic acid di-tert-butyl ester 5.072 g (yield 55.2%) as a white solid. 1H NMR (CDCl3) δ: 7.275 (2H, d, J=8.06 Hz), 7.161 (2H, d, J=8.05 Hz), 4.397 (1H, s), 2.344 (3H, s), 1.471 (18H, s) ppm. FABMS (+Ve), m/z 307 [MH+], 251 [MH+−C4H8], 195 [MH+−2C4H8]. Anal. calcd. for C18H26O4: C, 70.6; H, 8.6. Found: C, 70.34; H, 8.62.

Provenance & Evidence